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WO2020080848A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé - Google Patents

Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé Download PDF

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WO2020080848A1
WO2020080848A1 PCT/KR2019/013657 KR2019013657W WO2020080848A1 WO 2020080848 A1 WO2020080848 A1 WO 2020080848A1 KR 2019013657 W KR2019013657 W KR 2019013657W WO 2020080848 A1 WO2020080848 A1 WO 2020080848A1
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박형근
이선희
이윤석
김원삼
박정환
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DukSan Neolux Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50—Photovoltaic [PV] devices
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound for an organic electric element, an organic electric element using the same and an electronic device thereof.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on the function.
  • a difference in properties according to a material structure is very large, and thus, it is applied to various layers as a material for an organic electric device.
  • the band gap (HOMO, LUMO), electrical properties, chemical properties, physical properties, etc. have different characteristics depending on the number of rings, fused positions, and the type and arrangement of heteroatoms. This has been going on.
  • the LUMO and HOMO level of the host material are factors that greatly affect the efficiency and life of the organic electrical device. Accordingly, it is possible to control the charge balance in the light-emitting layer, quenching the dopant, and prevent the decrease in efficiency and life due to light emission at the hole transport layer interface.
  • TRTP PL lifetime
  • the TRTP (Time resolved transient PL) measurement method is a method of observing the decay time of the spectrum over time after irradiating a pulsed light source to the host thin film. It is a measurement method.
  • the TRTP measurement is a measurement method capable of distinguishing between fluorescence and phosphorescence, energy transfer method in mixed host material, exciplex energy transfer method, and TADF energy transfer method.
  • the present invention has been proposed to solve the above problems of the phosphorescent host material, charge balance control in the light emitting layer through the HOMO level adjustment for the host material of the phosphorescent dopant-containing organic electroluminescent device containing a phosphorescent dopant, and the efficiency, life span It is an object of the present invention to provide an organic electric device using the same compound and an electronic device thereof.
  • the present invention is to reduce the energy barrier between the light emitting layer and the adjacent layer by containing a specific second host material in combination with a specific first host material as a main component in order to control efficient hole injection in the light emitting layer of the phosphorescent organic electroluminescent device. It is possible to maximize the charge balance in the light emitting layer to provide high efficiency and high lifespan of the organic electric device.
  • the organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode
  • the organic material layer includes a light emitting layer
  • the light emitting layer is a phosphorescent light emitting layer
  • the present invention provides an organic electric device using the compound represented by the above formulas and an electronic device thereof.
  • the mixture according to the present invention as a phosphorescent host material, it is possible to achieve high luminous efficiency and low driving voltage of the organic electric device, and also significantly improve the life of the device.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • organic electrical element 110 substrate
  • first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, or order of the component is not limited by the term.
  • a component is described as being “connected”, “coupled” or “connected” to another component, that component may be directly connected to or connected to the other component, but another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.
  • halo or halogen as used herein are fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise noted.
  • alkyl or "alkyl group” used in the present invention has a single bond of 1 to 60 carbon atoms, unless otherwise specified, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycle.
  • radicals of saturated aliphatic functional groups including alkyl groups, cycloalkyl-substituted alkyl groups.
  • haloalkyl group or "halogenalkyl group” as used in the present invention means an alkyl group substituted with halogen unless otherwise specified.
  • heteroalkyl group used in the present invention means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.
  • alkenyl group used in the present invention have a double or triple bond of 2 to 60 carbon atoms, unless otherwise specified, and include straight or branched chain groups. , But is not limited to this.
  • cycloalkyl means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, but is not limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, and is limited thereto. It is not.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and 2 to 60 unless otherwise specified. It has a carbon number, and is not limited thereto.
  • aryloxyl group or "aryloxy group” used in the present invention means an aryl group to which an oxygen radical is attached, and has a carbon number of 6 to 60 unless otherwise specified, and is not limited thereto.
  • aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified.
  • an aryl group or an arylene group means a single ring or multi-ring aromatic, and includes an aromatic ring formed by adjacent substituents participating in a bond or reaction.
  • the aryl group may be a phenyl group, biphenyl group, fluorene group, dimethylfluorene group, diphenylfluorene group, or spirofluorene group.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • a radical substituted with an aryl group has a carbon number described herein.
  • arylalkoxy group it means an alkoxy group substituted with an aryl group
  • alkoxycarbonyl group it means a carbonyl group substituted with an alkoxyl group
  • arylcarbonyl alkenyl group it means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroalkyl means alkyl containing one or more heteroatoms, unless otherwise specified.
  • heteroaryl group or “heteroarylene group” means an aryl group or an arylene group having 2 to 60 carbon atoms, each of which contains one or more heteroatoms, unless otherwise specified. No, it includes at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
  • heterocyclic group used in the present invention includes at least one heteroatom, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, heteroaliphatic ring and hetero, unless otherwise specified. Aromatic rings. Adjacent functional groups may also be formed by bonding.
  • heteroatom refers to N, O, S, P or Si, unless otherwise stated.
  • heterocyclic group may include a ring containing SO 2 instead of carbon forming a ring.
  • heterocyclic group includes the following compounds.
  • aliphatic refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof, It contains a saturated or unsaturated ring.
  • hetero compounds or hetero radicals other than the above-described hetero compounds include one or more hetero atoms, but are not limited thereto.
  • carbonyl used in the present invention is represented by -COR ', where R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, 3 to 30 carbon atoms. Is a cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • ether used in the present invention is represented by -RO-R ', wherein R or R' are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or 6 to 30 carbon atoms. It is an aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • substituted in the term “substituted or unsubstituted” used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, substituted with deuterium C 6 ⁇ C 20 aryl group, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron Means a group, a germanium group, and one or more substituents selected from the group consisting of C 2 to C 20 heterocyclic groups, and is not limited
  • the substituent R 1 means non-existent, that is, when a is 0, it means that hydrogen is bonded to all of the carbons forming the benzene ring.
  • the formula or compound may be omitted.
  • a is an integer of 1
  • one substituent R 1 is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, each of them is bonded as follows, where R 1 may be the same or different from each other.
  • a is an integer of 4 to 6 it binds to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bound to the carbon forming the benzene ring is omitted.
  • the present invention is an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer. It provides an organic electric device comprising a first host compound represented by the formula (1) and a second host compound represented by the following formula (2).
  • X, Y, V and W are each independently O; S; CR'R "; SiR'R”; Se; Or NR ';
  • a, b, c and d are each independently 0 or 1, provided that a + b and c + d are 1 or more,
  • R 'and R are each independently selected from the group consisting of hydrogen; C 1 to C 50 alkyl group; C 6 to C 60 aryl group; and C 2 to C 60 heteroaryl group; or R 'And R "form a ring with each other to form a spiro ring,
  • L 1 , L 2 and L ' are each independently a single bond; C 6 ⁇ C 60 Arylene group; Or C 2 ⁇ C 60 heteroarylene group; is,
  • Ar 1 and Ar 2 are each independently hydrogen; heavy hydrogen; C 6 ⁇ C 60 Aryl group; Alkyl groups; C 2 ⁇ C 60 heteroaryl group; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-NR'R ";
  • Z is NR ', O, S, CR'R ", SiR'R", or Se,
  • R 1 to R 16 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of,
  • R a and R b are independently of each other C 6 ⁇ C 60 aryl group; Fluorenyl group; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; And O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom; is selected from the group consisting of,
  • l, n, o, p, and e are 2 or more, they are the same as or different from each other, and a plurality of R 1 , a plurality of R 3 , a plurality of R 4 , a plurality of R 5 , and a plurality of R 11 They may combine with each other to form an aromatic and heteroaromatic ring,
  • R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 12 and R 13 , R 14 and R 16 , R 16 and R 15 , R 15 and R 6 are bonded to each other to be aromatic and hetero Can form an aromatic ring,
  • a ring is a C 6 ⁇ C 60 aryl group or a C 2 ⁇ C 60 heteroaryl group
  • n, l and p are any integers from 0 to 4, m is 0 or 1, o is an integer from 0 to 3, e is an integer from 0 to 10,
  • the compound represented by the formula (1) in the present invention provides an organic electric device comprising a compound represented by the following formula (3) or (4).
  • the present invention provides an organic electric device in which the compound represented by the formula (1) includes a compound represented by any one of the following formulas (5) to (12).
  • the present invention provides an organic electric device including a compound in which all of l, m, n, o and p are 0 in the formula (1).
  • the present invention provides an organic electroluminescent device including a compound in which any one of the R 1 , R 3 , R 4 and R 5 in the formula (1) combines with each other to form a ring. .
  • the present invention in the formula (1), provides an organic electric device comprising a compound, each independently S or O.
  • the formula (1) in the present invention includes the following compound.
  • the present invention provides an organic electric device in which the compound represented by the formula (2) includes a compound represented by the following formula (13) or (14).
  • V, W, L 2 , Ar 2 , A, R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and e are the same as defined above ⁇
  • the present invention is a compound represented by the formula (2) R 6 and R 15 , R 15 and R 16 , R 16 and R 14 , R 12 and R 13 , R 7 and R 8 , R 8 and R 9 and R At least one pair of 9 and R 10 is bonded to each other to provide an organic electric device comprising a compound that forms an aromatic or heteroaromatic ring.
  • the present invention includes a compound represented by any one of the following formulas (15) to (38).
  • V, W, L 2 , Ar 2 , A, R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and e are as defined above.
  • the present invention provides an organic electric device in which the compound represented by the formula (2) includes a compound represented by any one of the following formulas (39) to (46).
  • L 2 , Ar 2 , A, R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R ', R "and e are as defined above.
  • the present invention is characterized in that R 6 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 and R 16 of the compound represented by the formula (2) are all hydrogen.
  • An organic electric device is provided.
  • the present invention provides an organic electric device comprising a compound represented by any one of the following (A-1) to (A-13) in the A ring in the formula (2).
  • the formula (2) in the present invention includes the following compound.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180 and a first electrode 120 and a second electrode formed on the substrate 110.
  • An organic material layer including the compound represented by Chemical Formula 1 is provided between (180).
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic material layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170 sequentially on the first electrode 120. At this time, layers other than the emission layer 150 may not be formed.
  • a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like may be further included, and the electron transport layer 160, etc. may also serve as a hole blocking layer.
  • the organic electric device according to the present invention may further include a protective layer formed on one surface opposite to the organic material layer among at least one surface of the first electrode and the second electrode.
  • the band gap, electrical properties, and interfacial properties may vary depending on which substituents are attached to which positions, so the selection of the core and the combination of sub-substituents coupled thereto are also very good. It is important, especially when the energy level and T1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.
  • the organic electroluminescent device may be manufactured using a physical vapor deposition (PVD) method.
  • PVD physical vapor deposition
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and an electron transport layer 160 are formed thereon.
  • After forming an organic material layer including the electron injection layer 170 it can be manufactured by depositing a material that can be used as a cathode thereon.
  • the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150
  • the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.
  • the present invention provides a compound represented by the formula (1) and the formula (2) in an ratio of any one of 1: 9 to 9: 1 to provide an organic electric device included in the light emitting layer, preferably Is 1: 9 to 5: 5, more preferably mixed in a ratio of 2: 8 to 3: 7 and included in the light emitting layer.
  • the present invention further comprises a light efficiency improving layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer from one side of the first electrode in the organic electric device.
  • a light efficiency improving layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer from one side of the first electrode in the organic electric device.
  • the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process, and the organic material layer according to the present invention can be formed by various methods Therefore, the scope of the present invention is not limited by the forming method.
  • the organic electric device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
  • WOLED White Organic Light Emitting Device
  • RGB Red
  • Green Green
  • B Blue
  • the R, G, and B light emitting units are arranged in a mutually planar side-by-side manner, and the stacking method in which the R, G, and B light-emitting layers are stacked up and down.
  • CCM color conversion material
  • the present invention is a display device comprising the above-described organic electric device; And a control unit for driving the display device.
  • the present invention provides an electronic device characterized in that the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.
  • the compound represented by the formula (1) according to the present invention (final product 1) is prepared by reacting one of Sub 1 and Sub 2 with Sub 3 as shown in Reaction Scheme 1 below.
  • the compound belonging to Sub 1 or Sub 2 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS value of the compound belonging to Sub 1 or Sub 2.
  • the compound belonging to Sub 3 may be the following compound, but is not limited thereto, and Table 2 shows the FD-MS value of the compound belonging to Sub 3.
  • Sub 1-7 (8.6g, 20mmol), Sub 3-3 (5.7g, 20mmol), Pd (PPh 3 ) 4 (0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL) / H 2 O (20mL) were obtained using the 1-2 synthesis method above to obtain products 1-7 (10.8g, 81%). .
  • the compound represented by Chemical Formula (2) according to the present invention (final product 2) is prepared by reacting Sub 4 and Sub 5 as shown in Reaction Scheme 4 below.
  • Sub 4 of Scheme 4 may be synthesized by the reaction route of Scheme 5 below, but is not limited thereto.
  • Sub 4 examples are as follows, but are not limited thereto, and Table 4 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 4.
  • -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a thickness of 60 nm.
  • NPB N, N'-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine
  • the hole blocking layer (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10 nm, and the electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm.
  • an organic electroluminescent device was manufactured by depositing LiF, an alkali metal halide as an electron injection layer, to a thickness of 0.2 nm, and then depositing Al to a thickness of 150 nm to use as a cathode.
  • the electroluminescence (EL) characteristics were measured by the PR-650 of photoresearch by applying a net bias DC voltage to the organic electroluminescent elements of the Examples and Comparative Examples prepared as described above, and the measurement result showed a reference luminance of 2500 cd / m 2 In the T95 life was measured by a life measurement equipment manufactured by Max Science. Table 7 below shows the results of device fabrication and evaluation.
  • An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 was used alone as a host.
  • An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 2 was used alone as a host.
  • An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 and Comparative Compound 1 were used as a mixture.
  • An organic electroluminescent device was manufactured in the same manner as in the above Example, except that the compound represented by Chemical Formula 2 and Comparative Compound 2 were used as a mixture.
  • An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 and Comparative Compound 3 to Comparative Compound 5 were used as a mixture.
  • the present inventors determined that the substance of the substance of Formula 1 and the substance of Formula 2 has new characteristics other than the characteristics of the substance, respectively, and the substance of Formula 1 and the substance of Formula 2 , PL lifetime was measured using each mixture of the present invention.
  • a new PL wavelength was formed unlike that of a single compound.
  • the increase was from about 60 times to as much as about 360 times less than the reduction and extinction time.
  • the compound of the present invention is used in combination, not only electrons and holes are moved through the energy level of each material, but also electrons, hole movement or energy due to exciplex of new regions having new energy levels formed due to mixing. It is judged that the efficiency and life of the furnace are increased.
  • the mixed thin film is an important example of exciplex energy transfer and luminescence processes.
  • the reason why the combination of the present invention is superior to Comparative Examples 7 to 11 used as a phosphorescent host in which a comparative compound is mixed is because of the polycyclic ring compound represented by Chemical Formula 2, which has characteristics such as stability to hole and high T1 as well as electron.
  • the compound represented by Chemical Formula 1 having strong hole characteristics is mixed, the electron blocking ability is improved due to the high T1 and high LUMO energy values, and more holes are quickly and easily moved in the light emitting layer.
  • the mixture of the compounds of the present invention was measured by fabricating the device by ratio (2: 8, 3: 7, 4: 6, 5: 5).
  • the results were described in detail, it was confirmed that as the second host ratio increased, the result of the driving voltage was further improved. Therefore, in the case of a mixture, it is judged that it is a very important task to derive a mixing ratio in which the charge balance in the light emitting layer is maximized because the amount of the mixing ratio affects the characteristics.
  • the present invention it is possible to manufacture an organic device having excellent device characteristics of high brightness, high light emission and high life, and thus there is industrial applicability.

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  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
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Abstract

La présente invention concerne un nouveau composé pouvant améliorer l'efficacité d'émission de lumière, la stabilité et la durée de vie d'un élément. L'invention concerne également un élément électrique organique l'utilisant et un dispositif électronique associé.
PCT/KR2019/013657 2018-10-17 2019-10-17 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé Ceased WO2020080848A1 (fr)

Applications Claiming Priority (2)

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